Heterocyclic Building Blocks-Pyrrolines

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-Methoxypiperidine(SMILESS: COC1CCNCC1,cas:4045-24-3) is researched.Safety of 3-Chloro-2,2-dimethylpropanoic acid. The article 《Identification of thiophene-benzenesulfonamide derivatives for the treatment of multidrug-resistant tuberculosis》 in relation to this compound, is published in European Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:4045-24-3).

A series of thiophene-benzenesulfonamide derivatives was designed and synthesized by exploring the structure-activity relationship of lead compounds 2,3-disubstituted thiophenes I and 297F II as antituberculosis agents, which displayed potent antimycobacterial activity against drug-susceptible and clin. isolated drug-resistant tuberculosis. In particular, compound III (-R1R2- = -(CH2)4-), which had improved activity (min. inhibitory concentration of 0.023 μg/mL) compared with the lead compounds, displayed good intracellular antimycobacterial activity in macrophages with a reduction of 1.29 log10 CFU. A druggability evaluation indicated that compound III (-R1R2- = -(CH2)4-) had favorable hepatocyte stability, low cytotoxicity, and low hERG channel inhibition. Moreover, compound III (-R1R2- = -(CH2)4-) exhibited modest in vivo efficacy in an acute mouse model of tuberculosis. In addition, the mol. docking study elucidated the binding mode of compound III (-R1R2- = -(CH2)4-) in the active site of DprE1. Therefore, compound III (-R1R2- = -(CH2)4-) may be a promising antituberculosis lead for further research.

Here is just a brief introduction to this compound(4045-24-3)Name: 4-Methoxypiperidine, more information about the compound(4-Methoxypiperidine) is in the article, you can click the link below.

Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Selective C-H Fluorination of Pyridines and Diazines Inspired by a Classic Amination Reaction, published in 2013-11-22, which mentions a compound: 34941-92-9, Name is 4-Chloro-2-fluoropyridine, Molecular C5H3ClFN, SDS of cas: 34941-92-9.

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochems., and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. The authors present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using com. available silver(II) fluoride. The reactions occur at ambient temperature within 1 h with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Larcheveque, Marc; Henrot, Serge researched the compound: (R)-4-Hydroxydihydrofuran-2(3H)-one( cas:58081-05-3 ).Name: (R)-4-Hydroxydihydrofuran-2(3H)-one.They published the article 《New chiral synthons. β,γ-Epoxy esters. Application to the synthesis of enantiomerically pure β-hydroxy esters》 about this compound( cas:58081-05-3 ) in Tetrahedron Letters. Keywords: hydroxy ester chiral; epoxy ester chiral synthon. We’ll tell you more about this compound (cas:58081-05-3).

The preparation of optically pure β,γ-epoxy esters I (R = H, Me) was achieved through the opening of 3-hydroxy butanolides II with trimethylsilyl iodide followed by cyclization with silver oxide. I react with organocuprates to afford β-hydroxy esters III (R1 = Me, Et, Bu, Me2C:CH, BuCH:CH) of high enantiomeric purity.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Synthetic Route of C9H9NO2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (2-Methylbenzo[d]oxazol-5-yl)methanol, is researched, Molecular C9H9NO2, CAS is 136663-38-2, about Design, synthesis and antimicrobial activity of novel 2-substituted benzoxazole derivatives. Author is Balaswamy, G.; Pradeep, P.; Srinivas, K.; Rajakomuraiah, T..

In the current research work, the title compounds were synthesized from Me 2-substituted benzoxazole-5-carboxylate by refluxing with methanol and THF (1 : 1) in presence of NaBH4, which afforded (2-substituted benzoxazol-5-yl)methanol, on partial oxidation with PCC furnished 2-substituted benzoxazole-5-carbaldehyde, on treatment with appropriate carbonyl compounds monoethyl malonate, Et acetoacetate or malonic acid yielded the corresponding α,β-unsaturated derivatives of 2-substituted benzoxazoles like, Et 3-(2-substituted benzoxazol-5-yl)acrylate, 4-(2-substituted benzoxazol-5-yl)but-3-en-2-one and 3-(2-substituted benzoxazol-5-yl)acrylic acid. The identification and characterization of all the synthesized compounds were confirmed by elemental anal., m.p., thin layer chromatog., FTIR, 1H NMR and mass spectral data. All the compounds were screened for antimicrobial activity. In view of interesting biol. activities and pharmacol. importance associated with benzoxazole derivatives, some of the derivatives of benzoxazole containing heterocyclic ring were prepared and their bio-potential were evaluated.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Computed Properties of C5H2Cl2FN. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2,6-Dichloro-3-fluoropyridine, is researched, Molecular C5H2Cl2FN, CAS is 52208-50-1, about Synthesis of fluorinated pyridines by the Balz-Schiemann reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid. Author is Matsumoto, Junichi; Miyamoto, Teruyuki; Minamida, Akira; Nishimura, Yoshiro; Egawa, Hiroshi; Nishimura, Haruki.

Fluorination of the 2,6-disubstituted 3-aminopyridines I (R = SEt, pyrrolidino, 4-ethoxycarbonylpiperazino, 4-acetylpiperazino, R1 = NHAc; R = R1 = Cl) by the Balz-Schiemann reaction gave 3-pyridinediazonium tetrafluoroborates which were heated with or without a solvent to give the corresponding fluorinated pyridines, in good yields. 2-Substituted 6-acetylamino-3-fluoropyridines were converted by a known method into a series of 7-substituted 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids including enoxacin (II).

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Pyrroline – Wikipedia,
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Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Chloro-5-iodo-3-methylpyridine, is researched, Molecular C6H5ClIN, CAS is 59782-89-7, about Some 2,5- and 5,6-dihalonicotinic acids and their precursors. IV.Reference of 2-Chloro-5-iodo-3-methylpyridine.

The pyridinecarboxylic acids I (R = Cl, R1 = CO2H, R2 = Cl, iodo; R = Cl, R1 = Cl, iodo, R2 = CO2H) were prepared by oxidation of I (R = Cl, R1 = Me, R2 = Cl, iodo; R = Cl, R1 = Cl, iodo, R2 = Me; resp.), which were prepared by diazotization and substitution of I (R = Cl, R1 = Me, R2 = NH2; R = Cl, R1 = NH2, R2 = Me; resp.). I (R = R1 = Cl, R2 = CO2H) and NaI gave I (R = iodo, R1 = Cl, R2 = CO2H).

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Pyrroline – Wikipedia,
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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 4045-24-3, is researched, SMILESS is COC1CCNCC1, Molecular C6H13NOJournal, Article, Research Support, Non-U.S. Gov’t, Journal of Medicinal Chemistry called An Exploration of Chemical Properties Required for Cooperative Stabilization of the 14-3-3 Interaction with NF-κB-Utilizing a Reversible Covalent Tethering Approach, Author is Wolter, Madita; Valenti, Dario; Cossar, Peter J.; Hristeva, Stanimira; Levy, Laura M.; Genski, Thorsten; Hoffmann, Torsten; Brunsveld, Luc; Tzalis, Dimitrios; Ottmann, Christian, the main research direction is reversible covalent PPI stabilizer NFkB p65 complex mol glue.Related Products of 4045-24-3.

Protein-protein modulation has emerged as a proven approach to drug discovery. While significant progress has been gained in developing protein-protein interaction (PPI) inhibitors, the orthogonal approach of PPI stabilization lacks established methodologies for drug design. Here, we report the systematic ”bottom-up” development of a reversible covalent PPI stabilizer. An imine bond was employed to anchor the stabilizer at the interface of the 14-3-3/p65 complex, leading to a mol. glue 24j (I) that elicited an 81-fold increase in complex stabilization. Utilizing protein crystallog. and biophys. assays, we deconvoluted how chem. properties of a stabilizer translate to structural changes in the ternary 14-3-3/p65/mol. glue complex. Furthermore, we explore how this leads to high cooperativity and increased stability of the complex.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Renk, Dana R.; Skraban, Marcel; Bier, Dirk; Schulze, Annette; Wabbals, Erika; Wedekind, Franziska; Neumaier, Felix; Neumaier, Bernd; Holschbach, Marcus published the article 《Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands》. Keywords: morpholinyl benzothiazolyl methylpiperidine carboxamide preparation adenosine receptor fluorine isotopologue; A(2A) adenosine Receptor; Autoradiography; Binding studies; Fluorinated analogues; Fluorine-18 isotopologues; Ligand synthesis.They researched the compound: 4-Methoxypiperidine( cas:4045-24-3 ).HPLC of Formula: 4045-24-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:4045-24-3) here.

With the aim to obtain potent adenosine A2A receptor (A2AR) ligands, a series of eighteen derivatives of 4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-1,3-benzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide were designed and synthesized. The target compounds were obtained by a chem. building block principle that involved reaction of the appropriate aminobenzothiazole Ph carbamates with either com. available or readily synthesized functionalized piperidines. Ki values for human A2AR ranged from 2.4 to 38 nM, with more than 120-fold selectivity over A1 receptors for all evaluated compounds except 4-Fluoro-4-(hydroxymethyl)-N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)piperidine-1-carboxamide which had a Ki of 361 nM and 18-fold selectivity. The most potent fluorine-containing derivatives exhibited Ki values of 4.9 nM, 3.6 nM and 2.8 nM for the human A2AR. Interestingly, the corresponding values for rat A2AR were found to be four to five times higher. Their binding to A2AR was further confirmed by radiolabeling with 18F and in vitro autoradiog. in rat brain slices, which showed almost exclusive striatal binding and complete displacement by the A2AR antagonist ZM 241385. Authors conclude that these compounds represent potential candidates for the visualization of the A2A receptor and open pathways to novel therapeutic treatments of neurodegenerative disorders or cancer.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Application In Synthesis of 4-Chloro-2-fluoropyridine. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-Chloro-2-fluoropyridine, is researched, Molecular C5H3ClFN, CAS is 34941-92-9, about Tetrahydrofuran-Based Transient Receptor Potential Ankyrin 1 (TRPA1) Antagonists: Ligand-Based Discovery, Activity in a Rodent Asthma Model, and Mechanism-of-Action via Cryogenic Electron Microscopy. Author is Terrett, Jack A.; Chen, Huifen; Shore, Daniel G.; Villemure, Elisia; Larouche-Gauthier, Robin; Dery, Martin; Beaumier, Francis; Constantineau-Forget, Lea; Grand-Maitre, Chantal; Lepissier, Luce; Ciblat, Stephane; Sturino, Claudio; Chen, Yong; Hu, Baihua; Lu, Aijun; Wang, Yunli; Cridland, Andrew P.; Ward, Stuart I.; Hackos, David H.; Reese, Rebecca M.; Shields, Shannon D.; Chen, Jun; Balestrini, Alessia; Riol-Blanco, Lorena; Lee, Wyne P.; Liu, John; Suto, Eric; Wu, Xiumin; Zhang, Juan; Ly, Justin Q.; La, Hank; Johnson, Kevin; Baumgardner, Matt; Chou, Kang-Jye; Rohou, Alexis; Rouge, Lionel; Safina, Brian S.; Magnuson, Steven; Volgraf, Matthew.

Transient receptor potential ankyrin 1 (TRPA1) is a nonselective calcium-permeable ion channel highly expressed in the primary sensory neurons functioning as a polymodal sensor for exogenous and endogenous stimuli and has generated widespread interest as a target for inhibition due to its implication in neuropathic pain and respiratory disease. Herein, we describe the optimization of a series of potent, selective, and orally bioavailable TRPA1 small mol. antagonists, leading to the discovery of a novel tetrahydrofuran-based linker. Given the balance of physicochem. properties and strong in vivo target engagement in a rat AITC-induced pain assay, compound (I) was progressed into a guinea pig ovalbumin asthma model where it exhibited significant dose-dependent reduction of inflammatory response. Furthermore, the structure of the TRPA1 channel bound to compound (II) was determined via cryogenic electron microscopy to a resolution of 3 Å, revealing the binding site and mechanism of action for this class of antagonists. Tetrahydrofurans

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

HPLC of Formula: 58081-05-3. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols and Their Structural Revisions. Author is Sunnapu, Ranganayakulu; Rajendar, Goreti.

A concise, stereoselective and protecting group free approaches for the total synthesis of (-)-(2S,4R)- and (+)-(2R,4S)-3′-methoxyl citreochlorols, e.g., I, and their stereoisomers are demonstrated. All four stereoisomers were synthesized to establish the absolute stereochem. of the reported structures and the structures were revised accordingly. The approach involves chelation controlled regioselective reduction of a diester, silyl iodide promoted ring-opening iodo esterification of lactones, highly chemo- and regioselective ring-opening of an epoxy ester, dichloromethylation of a carboxyl group, and syn- and anti-selective reduction of the resulted β-hydroxy ketone as key steps.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem